119566-46-0Relevant academic research and scientific papers
Cooperative copper-squaramide catalysis for the enantioselective N-H insertion reaction with sulfoxonium ylides
Burtoloso, Antonio C. B.,Echemendía, Radell,Furniel, Lucas G.
, p. 7453 - 7459 (2021)
The first examples of a highly efficient and enantioselective carbene-mediated insertion reaction, from a sulfur ylide, are described. By way of a catalytic asymmetric insertion reaction into N-H bonds from carbonyl sulfoxonium ylides and anilines, using a copper-bifunctional squaramide cooperative catalysis approach, thirty-seven α-arylglycine esters were synthesized in enantiomeric ratios up to 92?:?8 (99?:?1 after a single recrystallization) and reaction yields ranging between 49-96%. Furthermore, the protocol benefits from quick reaction times and is conducted in a straightforward manner.
Visible-light-promoted nitrone synthesis from nitrosoarenes under catalyst- and additive-free conditions
Cai, Bao-Gui,Li, Lin,Xiao, Wen-Jing,Xu, Guo-Yong,Xuan, Jun
, p. 823 - 829 (2021)
A green and sustainable nitrone formation reaction via visible-light-promoted reaction of aryl diazoacetates with nitrosoarenes is described. This protocol exhibits good functional group tolerance and broad substrate scope for both aryl diazoacetates with nitrosoarenes. Comparing the reported methods for the synthesis of nitrones from nitrosoarenes, the reaction described herein occurs under sole visible-light irradiation without the need of any catalysts and additives. Graphic abstract: [Figure not available: see fulltext.]
Asymmetric intermolecular N-H insertion reaction of phenyldiazoacetates with anilines catalyzed by achiral dirhodium(II) carboxylates and cinchona alkaloids
Saito, Hiroaki,Uchiyama, Taketo,Miyake, Muneharu,Anada, Masahiro,Hashimoto, Shunichi,Takabatake, Tohru,Miyairi, Shinichi
, p. 1149 - 1155 (2010)
Asymmetric N-H insertion of phenyldiazoacetates with anilines catalyzed cooperatively by achiral dirhodium(II) carboxylates and cinchona alkaloids is described. A new catalytic system of dirhodium(II) tetrakis(triphenylacetate), Rh2(TPA)4
Silver-catalyzed three-component reaction of phenyldiazoacetate with arylamine and imine
Chen, Bai-Ling,Wang, Zhen,Zhang, You-Can,Zhao, Zhi-Gang,Chen, Zili
, p. 1594 - 1598 (2018)
A new method was developed to diastereoselectively synthesize polysubstituted 1,2-diamine compounds from the reaction of diazoesters with arylamines and diaryl imines by using the dioxazoline ligand L2-ligated silver catalyst. The Lewis acidity of the silver catalyst affected the different types of substrate diastereoselectivities; It also led to the formation of amine-exchange side products.
N-H and S-H insertions over Cu(I)-zeolites as heterogeneous catalysts
Saha, Pipas,Jeon, Himchan,Mishra, Pratyush Kumar,Rhee, Hyun-Woo,Kwak, Ja Hun
, p. 10 - 18 (2016)
N-H and S-H insertion reactions of α-diazoesters into amines and thiols were conducted using various Cu(I)-zeolites, such as zeolite Y, Y USY, ZSM-5, and beta. All the Cu(I)-zeolites successfully catalyzed N-H insertion reactions with high product yields
A Novel Three-Component Reaction Catalyzed by Dirhodium(II) Acetate: Decomposition of Phenyldiazoacetate with Arylamine and Imine for Highly Diastereoselective Synthesis of 1,2-Diamines
Wang, Yuanhua,Zhu, Yanxin,Chen, Zhiyong,Mi, Aiqiao,Hu, Wenhao,Doyle, Michael P.
, p. 3923 - 3926 (2003)
(Matrix presented) A practical highly diastereoselective synthesis of 1,2-diamines through carbon-carbon bond formation involving an ammonium ylide intermediate is reported for the first time. By treating methyl phenyldiazoacetate with arylamine and imine in the presence of dirhodium acetate, the erythro diastereomer of methyl 1,2-diaryl-1,2-diaminopropanoate is formed with stereochemical preferences greater than 10:1.
Transfer hydrogenation of imines with carboxyl-tailed benzothiazoline as readily removable hydrogen donor
Zhu, Chen,Akiyama, Takahiko
, p. 416 - 418 (2012)
A benzothiazoline bearing 4-carboxyphenyl group at 2-position was developed as an efficient hydrogen donor for the transfer hydrogenation reaction. Introduction of the carboxyl group significantly facilitated the removal of the residual benzothiazoline an
Modular construction of multifunctional ligands for the enantioselective ruthenium-catalyzed carbenoid N-H insertion reaction:An enzyme-like and substrate-sensitive catalyst system
Huang, Wei-Sheng,Xu, Zheng,Yang, Ke-Fang,Chen, Li,Zheng, Zhan-Jiang,Xu, Li-Wen
, p. 46455 - 46463 (2015)
It was found for the first time that cinchonine- and BINOL-derived multifunctional ligands bearing a silicon-based bulky group exhibited promising enantioselective control in the ruthenium-catalysed carbenoid N-H insertion reaction, in which the Ru-L26 sy
New tandem reactions of metal carbenoids. Intermolecular formation of azomethine ylide from methyl 2-diazo-2-phenylacetate and schiff base: Intramolecular 1,3-dipolar cycloaddition
Khlebnikov,Novikov,Bespokoev,Kostikov,Kopf,Starikova,Antipin
, p. 922 - 932 (2005)
Rhodium acetate-catalyzed decomposition of methyl 2-diazo-2-phenylacetate in the presence of substituted N-methylbenzylideneamines possessing an activated alkenyl fragment (dipolarophile) in the side chain gives products of intramolecular cycloaddition of
Stereoretentive N-Arylation of Amino Acid Esters with Cyclohexanones Utilizing a Continuous-Flow System
Ichitsuka, Tomohiro,Komatsuzaki, Shingo,Masuda, Koichiro,Koumura, Nagatoshi,Sato, Kazuhiko,Kobayashi, Shū
, p. 10844 - 10848 (2021/05/31)
The N-arylation of chiral amino acid esters with minimal racemization is a challenging transformation because of the sensitivity of the α-stereocenter. A versatile synthetic method was developed to prepare N-arylated amino acid esters using cyclohexanones as aryl sources under continuous-flow conditions. The designed flow system, which consists of a coil reactor and a packed-bed reactor containing a Pd(OH)2/C catalyst, efficiently afforded the desired N-arylated amino acids without significant racemization, accompanied by only small amounts of easily removable co-products (i. e., H2O and alkanes). The efficiency and robustness of this method allowed for the continuous synthesis of the desired product in very high yield and enantiopurity with high space-time yield (74.1 g L?1 h?1) and turnover frequency (5.9 h?1) for at least 3 days.
